It’s that time of year again.
Companies have fresh budgets allocated. New territories carved out. Headcount approvals signed off. And recruiters are back on the hunt for new talent.
Every January, LinkedIn sees the biggest spike in job postings. But not all sales jobs are created equal.
So in this week’s issue, we’ll break down 5 critical things every salesperson should check before considering a new role – so you don’t end up job hopping five times in two years.
FEATURE
1/ Why they’re hiring
Companies hire reps for different reasons.
Some have an insatiable demand and need reps to close deals that are already coming in (think Zoom during Covid).
Others have a demand problem and need true hunters to create pipeline from scratch.
Neither is inherently good or bad, but each requires a very different skill set. Before moving forward, make sure you know which game you’re signing up to play.
2/ Who you’d be selling to
Selling to mom and pop restaurant owners is wildly different from selling to CIOs at Fortune 500 companies – even if it’s the same product.
Who you sell to will define your day to day. So before you take on a new role, be sure you can answer these questions:
What does the ICP for your territory look like?
Is what you’d be selling a must have or nice to have?
Is this a group of people you want to spend your days selling to?
3/ Attainment (not OTE)
OTE is fake news. Unless it’s backed by attainment.
Many companies use flashy OTEs to attract talent. But that's not the full picture. There are far better indicators of your earning potential:
The percentage of reps who hit quota.
What top and bottom performers actually take home.
Ramp length and whether the draw is guaranteed or recoverable.
Ideally, you want to be an elite rep in a role where even a below-average rep can crush it.
Pro tip: Some senior reps even ask recruiters for anonymized proof of earnings to verify what reps actually make.
4/ Team sentiment
A toxic manager and a team with low morale will kill your ability to perform.
Do a vibe check by connecting with current reps on LinkedIn and asking about their experience.
High churn is a red flag. So use Sales Navigator’s “Past Company” filter to see how many reps have left in the last 6-12 months. Reach out and ask why they left.
Pro tip: Reps fired for poor performance rarely have glowing things to say. Listen to all feedback, but don’t take every word as gospel.
5/ Upward Mobility
Upward mobility matters if you’re serious about growing your career (since you’re reading Stacked Seller, it’s probably important to you).
A growing company should reward merit. If no reps have been promoted in years, what are the odds you'll be the exception?
Here’s one way to check: Use Sales Navigator's "Previous Job Title" and "Current Company" filters to find people who previously held your target role. See where they are now. If many got promoted to senior IC or management roles, that’s a strong sign.
Pro tip: Some companies rebrand titles every few years. Watch for title changes that look like promotions but are really just vanity updates.
No company is perfect. You’d be hard pressed to find everything positive and no negatives. But you want to minimize risk and know what you’re getting yourself into.
Because as the saying goes, what boat you’re in is far more important than how hard you row.
YOUR TWO CENTS
➡ Are you considering a new role in 2026?
Actively interviewing
Casually looking
Not yet, but open to the right opportunity
No, staying put
*Reply with your number. I’ll share the poll results in the next issue.
LAST WEEK’S POLL RESULTS
➡ What's your 2026 quota compared to 2025?
Higher - 45%
About the same - 30%
Lower (lucky me) - 5%
Don't know yet - 20%
